Synthesis of N‑Oxyureas by Substitution and Cope-Type Hydroamination Reactions Using O‑Isocyanate Precursors

Oxy-carbamate O-isocyanate precursors facilitate access to synthetically valuable N-oxyureas via substitution with amines. This work exploits the reactivity of suitable O-isocyanate precursors, identified by a thorough study highlighting the different reactivity of isocyanate masking groups. This le...

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Bibliographic Details
Published inOrganic letters Vol. 19; no. 24; pp. 6574 - 6577
Main Authors Allen, Meredith A, Ivanovich, Ryan A, Polat, Dilan E, Beauchemin, André M
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 15.12.2017
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ALKENES
HYDROXYLAMINES
HYDROXYUREAS
HYDROXAMIC ACIDS
ELECTROPHILIC AMINATION
HISTONE-DEACETYLASE INHIBITORS
LOSSEN REARRANGEMENTS
ALKYNES
DERIVATIVES
BLOCKED ISOCYANATES
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Summary:Oxy-carbamate O-isocyanate precursors facilitate access to synthetically valuable N-oxyureas via substitution with amines. This work exploits the reactivity of suitable O-isocyanate precursors, identified by a thorough study highlighting the different reactivity of isocyanate masking groups. This led to bench-stable O-isocyanate precursors, offering improved versatility in the synthesis of N-oxyureas, and demonstrates the controlled reactivity of masked O-isocyanates. Suitable precursors also enabled the first example of Cope-type hydroamination of unsaturated hydroxyureas.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.7b03288